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A3555

Sigma-Aldrich

Arachidonic acid

from Porcine liver, BioReagent, suitable for cell culture, ≥99% (GC)

Sinônimo(s):

cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte

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About This Item

Fórmula linear:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
Número CAS:
506-32-1
Peso molecular:
304.47
Beilstein:
1713889
Número CE:
208-033-4
Número MDL:
MFCD00004417
Código UNSPSC:
12352200
ID de substância PubChem:
24890784

fonte biológica

Porcine liver

linha de produto

BioReagent

Ensaio

≥99% (GC)

Formulário

liquid

técnica(s)

cell culture | mammalian: suitable

cor

clear colorless to very faintly yellow

índice de refração

n20/D 1.4872 (lit.)

p.e.

169-171 °C/0.15 mmHg (lit.)

pf

−49 °C (lit.)

solubilidade

absolute ethanol: 10 mg/mL

densidade

0.922 g/mL at 25 °C (lit.)

Condições de expedição

dry ice

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

InChI

1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

chave InChI

YZXBAPSDXZZRGB-DOFZRALJSA-N

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Ações bioquímicas/fisiológicas

Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Embalagem

Sealed ampule.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

235.4 °F - closed cup

Ponto de fulgor (°C)

113 °C - closed cup

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Certificados de análise (COA)

Lot/Batch Number
SLBK8783V
SLBH2583V
SLBD9828V
SLBB9784V
071M1333V

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Zhuoming Liu et al.
The Journal of biological chemistry, 281(23), 16043-16051 (2006-04-15)
Dbs was identified in a cDNA-based expression screen for sequences that can cause malignant growth when expressed in murine fibroblasts. In previous studies we have shown that Dbs is a Rho-specific guanine nucleotide exchange factor that can activate RhoA and/or
Ninna Struck Rossen et al.
PloS one, 6(9), e25196-e25196 (2011-10-04)
Cell adhesion and migration are essential for the evolution, organization, and repair of living organisms. An example of a combination of these processes is the formation of new blood vessels (angiogenesis), which is mediated by a directed migration and adhesion
Song Xu et al.
Journal of virology, 86(23), 13025-13037 (2012-09-28)
Similar to other positive-sense, single-stranded RNA viruses, hepatitis C virus (HCV) replicates its genome in a remodeled intracellular membranous structure known as the membranous web (MW). To date, the process of MW formation remains unclear. It is generally acknowledged that
Donghui Liu et al.
American journal of physiology. Cell physiology, 301(3), C739-C748 (2011-07-08)
High-density lipoprotein (HDL) can induce cyclooxygenase-2 (COX-2) expression and prostacyclin I-2 (PGI-2) release in endothelial cells to exert multiple antiatherogenic functions. This effect has been attributed mainly to the role of sphingosine-1-phosphate (S1P) integrated in HDL. However, whether apolipoprotein A-I
Akinobu Hayashi et al.
Oncology letters, 8(4), 1513-1518 (2014-09-10)
Transforming growth factor β1 (TGFβ1) regulates a variety of cellular functions, including cell growth, apoptosis and differentiation. The aim of the current study was to investigate the alterations of phenotypic events in the long-term exposure of prostate cancer (PCa) cells
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